Synthesis and Complex Formation of Substituted Amino-p-chlorophenylglyoximes of Unsymmetrical vic-Dioximes

Abstract

In this study, anti-p-chlorophenylchloroglyoxime (C₈H₆Cl₂N₂O₂) has been synthesized by chlorination of anti-p-chlorophenylglyoxime. The reaction of C₈H₆Cl₂N₂O₂ with p-chloroaniline, o-toluidine, 1-naphthylamine and benzidine in ethanol between -10°C and -15°C gives unsymmetrical vic-dioximes, namely, p-chloroanilino-p-chlorophenylglyoxime(C₁₄H₁₁Cl₂N₃O₂), o-toluidino-p-chlorophenylglioxime (C₁₅H₁₄ClN₃O₂), 1-naphtylamino-p-chlorophenylglioxime (C₁₈H₁₄ClN₃O₂), 1,1′-biphenyl-4-amino-4′-amino-p-chlorophenylglioxime (C₂₀H₁₇ClN₄O₂). The Ni(II) and Cu(II) complexes of these ligands are square-planer while the Co(II) complexes are octahedral with water molecules as axial ligands. ¹H-NMR, AAS, IR spectra and elemental analyses data are given.